α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri

Füsun Şeyma Güngör; Ayşe Özdemir

doi:10.31466/kfbd.1393378

TR EN

α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri

Öz

α,β-Konjuge enon bileşikleri ile 2-diazo-5,5-dimetil-1,3-heksandionun dirodyum tetraasetat (Rh2(OAc)4) katalizörlüğünde tepkimeleri gerçekleştirilmiştir. Elde edilen ürünlerin yapıları FT-IR, GC-MS ve 1H NMR ve 13C NMR yöntemleri ile karakterize edilmiştir. Çalışmada kullanılan ilk α,β-konjuge enon bileşiği olan 3-metiliden-bisiklo[2.2.1]heptan-2-onun tepkimesinden 6,6-dimetil-3,5,6,7-tetrahidro-4H-spiro[benzofuran-2,2’-bisiklo[2.2.1]heptan]-3’,4-dion bileşiği tek ürün olarak elde edilmiştir. İkinci α,β-konjuge enon bileşiği olan 1-morfolinoprop-2-en-1-on Rh-karbeni ile tepkime vermemiş olup bu tepkimeden sadece karben dimeri elde edilmiştir.

Anahtar Kelimeler

Diazodikarbonil, Konjuge Enon, Dihidrofuran, Rh2(OAc)4

Destekleyen Kurum

İ.T.Ü. Bilimsel Araştırmalar Proje Birimi

Proje Numarası

İTÜ-Bap proje ID-kod 9039-1819

Etik Beyan

Yapılan çalışmada araştırma ve yayın etiğine uyulmuştur.

Teşekkür

Bu çalışma İ.T.Ü. Bilimsel Araştırmalar Proje Birimi tarafından (Proje no: İTÜ-Bap proje ID-kod 9039-1819) desteklenmiştir.

Kaynakça

Anac, O., and Daut, A. (1997). Reactions of α,β-enones with diazo compounds. Part 2: Synthesis of dihydrofuran derivatives. Liebigs Annalen / Recuil, 6, 1249-1254. doi: https://doi.org/10.1002/jlac.199719970630
Anac, O., Daut-Ozdemir, A., and Sezer, O. (2003). Reactions of α,β-enones with diazo compounds. Part 3: On the natüre of the 1,5-ring closure of α,β-enone ylides. Helvetica Chimica Acta, 86(2), 290-298. doi: https://doi.org/10.1002/hlca.200390030
Anac, O., Gungor, F. S., Kahveci, C., and Cansever, M. S. (2004). Reactions of α,β-enones with diazo compounds. Part 4: Reaction pathways from (Z)- and (E)- α,β-enones with dimethyl diazo malonate. Helvetica Chimica Acta, 87(2), 408-415. doi: https://doi.org/10.1002/hlca.200490039
Anac, O., and Gungor, F. S. (2010). Electrocyclization reactions of vinyl, styryl, and butadienyl conjugated carbonyl/azomethine ylides. Tetrahedron, 66, 5931-5953. doi: https://doi.org/10.1016/j.tet.2010.05.058
Celik, M. A., Yurtsever, M., Tuzun, N. S., Gungor, F. S., Sezer, O., and Anac, O. (2007). Metal-catalyzed cyclization reactions of carbonyl ylides: Synthesis and DFT study of mechanisms. Organometallics, 26(12), 2978-2985. doi: https://doi.org/10.1021/om0609970
Chapyshev, S. V., Nakano, H., and Ibata, T. (1996). Formal C-H insertion of diketocarbene generated by rhodium(II)-catalyzed decomposition of diazodimedone into a benzene molecule. Russian Chemical Bulletin, 45, 471-473. doi: https://doi.org/10.1007/BF01434000
Cornell, R., Scavo, F., Helquist, P., and Akermark, B. (1986). Functionalized oxazoles from rhodium(II)-catalyzed reaction of dimethyl diazomalonate with nitriles. Tetrahedron Letters, 27(46), 5559-5562. doi: https://doi.org/10.1016/S0040-4039(00)85265-X
Davies, H. M. L., and Romines, K. R. (1988). Direct synthesis of furan by 3 + 2 cycloaddition between rhodium(II) acetate stabilized carbenoids and acetylenes. Tetrahedron, 44(11), 3343-3348. doi: https://doi.org/10.1016/S0040-4020(01)85968-8
Daut-Ozdemir, A., Anaç, O., and Somer, M. (2002). Crystal Structure of 3R(S)-1'S(R)-2,2-Dimethoxycarbonyl-3-(2',6',6'-trimethyl-2'-cyclo¬hexen-1'-yl)2,3-dihydrofuran, C18H26O5. Zeitschrift für Kristallographie- New Crystal Structures, 217, 607-608. doi: https://doi.org/10.1524/ncrs.2002.217.jg.607
Dean, F. M. (1982). Advances in Heterocyclic Chemistry. In A. R. Katritzky (Ed.), (Vol 30, pp. 167-238). New York NY: Academic Press.

Dean, F. M., and Sargent, M. V. (1984). Comprehensive Heterocyclic Chemistry. In C. W. Bird and G. W. H. Cheeseman (Eds.) (Vol 4, pp. 531-598). NY: Pergamon Press.
Doyle, M. P., McKervey, T., and Ye, T. (1988). Modern catalytic methods for organic synthesis with diazo compounds. New York: Wiley
Gungor, F. S., Anac, O., and Sezer, O. (2011). Synthesis of naphthalenone, dihydroquinoline, and dihydrofuran derivatives. Helvetica Chimica Acta, 94(6), 1115-1129. doi: https://doi.org/10.1002/hlca.201000386
Gungor, F. S., Merey, G., and Anac, O. (2020). Chemoselective carbenoid reactions of furan/thiophene/pyrrole ring containing carbonyl and conjugated carbonyl at their 2-positions. ChemistrySelect, 5, 5337-5340. doi: 10.1002/slct.202000584
Jaques, R., Pal, R., Parker, N. A., Sear, C. E., Smith, P. W., Ribaucourt, A., and Hodgson, D. M. (2016). Recent applications in natural product synthesis of dihydrofuran and pyran formation by ring-closing alkene metathesis. Organic & Biomolecular Chemistry, 14, 5875-5893. doi: https://doi.org/10.1039/C6OB00593D
Kilroy, T. G., O’sullivan, T. P., and Guiry, P. J. (2005). Synthesis of dihydrofurans substituted in the 2-position. European Journal of Organic Chemistry, 23, 4929-4949. doi: https://doi.org/10.1002/ejoc.200500489
Kışkan, F. Ş. (2023). Copper-catalyzed reactions of β-alkoxy/phenoxy enones with dimethyl diazomalonate. Turkish Journal of Chemistry, 47(1), 81-87. doi: 10.55730/1300-0527.3519
Konnur, S. B., and Nandibewoor, S. T. (2019). Kinetic investigations of ruthenium(III) catalyzed oxidation of dimedone by diperiodatocuprate(III) in aqueous alkaline media. Russian Journal of Physical Chemistry A, 93(9), 1686-1698. doi: https://doi.org/10.1134/S003602441909022X
Lee, Y. R., and Suk, J. Y. (1998). Efficient synthesis of β-substituted α-chloro enones by rhodium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with acid chlorides. Chemical Communications, 2621-2622. doi: https://doi.org/10.1039/A806993J
Lee, Y. R., Suk, J. Y., and Kim, B. S. (1999). Rhodium(II)-catalyzed reactions of 3-diazo-2,4-chromenediones. First one-step synthesis of pterophyllin 2. Tetrahedron Letters, 36(3), 6603-6607. doi: https://doi.org/10.1016/S0040-4039(99)01317-9
Lee, Y. R., Suk, J. Y., and Kim, B. S. (1999). Efficient synthesis of oxindoles by thermal and rhodium(II)-catalyzed Wolff rearrangement. Tetrahedron Letters, 40(17), 8219-8221. doi: https://doi.org/10.1016/S0040-4039(99)01714-1
Lee, Y. R., and Kim, D. H. (2001). Novel method fort he synthesis of β-substituted α-haloenones by rhodium(II)-catalyzed reactions of diazodicarbonyl compounds with benzyl halides. Tetrahedron Letters, 42(37), 6561-6563. doi: https://doi.org/10.1016/S0040-4039(01)01345-4
Lee, Y. R., and Suk, J. Y. (2002). Efficient synthesis of dihydrofurans and furans by rhodium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds. Tetrahedron, 58(12), 2359-2367. doi: https://doi.org/10.1016/S0040-4020(02)00118-7
Lee, Y. R., Cho, B. S., and Kwon, H. J. (2003). A convinient and efficient preparation of β-substituted α-haloenones from diazdicarbonyl compounds. Tetrahedron, 59(47), 9333-9347. doi: https://doi.org/10.1016/j.tet.2003.09.087
Lee, Y. R., Hwang J. C. (2005). Efficient synthesis of five-and seven-membered-ring heterocycles by rhodium(II)-catalyzed [3+2] and [3+4] cycloaddition of diazodicarbonyl compounds with conjugated dienes. European Journal of Organic Chemistry, 1568-1577. doi: https://doi.org/10.1002/ejoc.200400452
Padwa, A., and Kinder, F. R. (1993). Rhodium(II)-catalyzed cyclization of 2-alkynyl 2-diazo-3-oxobutanoates as a method for synthesizing substituted furans. Journal Of Organic Chemistry, 58(1), 21-28. doi: https://doi.org/10.1021/jo00053a009
Regitz, M., and Stadler, D. (1965). Reaktionen aktiver methylenverbindungen mit Aziden VIII. Über α,α'-azo-β-dicarbonylverbindungen bzw . deren tautomere. Ein beitrag aliphatischen azokupplung. Justus Liebigs Annalen der Chemie, 687(1), 214-231. doi: https://doi.org/10.1002/jlac.19656870120
Shevchenko, V. V., Shakhmin, A. A., and Nikolaev, V. A. (2006). Catalytic decomposition of 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dione and its analogs. Russian Journal of Organic Chemistry, 42, 1741-1744. doi: https://doi.org/10.1134/S1070428006110273
Shi, G., and Xu, Y. (1989). Ethyl 3-trifluoro-2-diazo-propionate as a potentially useful CF3-containing building block: Preparation and [Rh(OAc)2]2-catalysed reaction with nitriles. Journal of the Chemical Society, Chemical Communications, 607-608. doi: 10.1039/C39890000607
Slavinskaya, V. A., Karakhanov, R. A., Brezhnev, L. Y., Geiman, I. I., Bulenkova, L. F., and Strautinya, A. K. (1982). Catalytic synthesis of dihydrofurans. Chemistry of Heterocyclic Compounds, 18, 997-1008. doi: https://link.springer.com/article/10.1007/BF00503178
Spencer, T. A., Villarica, R. M., Storm, D. L., Weaver, T. D., Friary, R. J., Posler, J., Shafer, P. R. (1967). Total synthesis of racemic methyl vinhaticoate. Journal of American Chemical Society, 89(21), 5497-5499. doi: https://doi.org/10.1021/ja00997a060
Storm, D. L., and Spencer, T. A. (1967). Furan synthesis by 1,4 addition of carboethoxycarbene to α-methoxymethylene ketones. Tetrahedron Letters, 8(20), 1865-1867. doi: https://doi.org/10.1016/S0040-4039(00)90743-3
Ye, T., and, McKervey, M. A. (1994). Organic synthesis with alpha-diazo carbonyl compounds. Chemical Reviews, 94, 1091-1160. doi: https://doi.org/10.1021/cr00028a010
Zheng, J.-C., Zhu, C.-Y., Sun, X.-L., Tang, Y., and Dai, L.-X. (2008). Highly diastereoselective and enantioselective formal [4+1] ylide annulation for the synthesis of optically active dihydrofurans. Journal of Organic Chemistry, 73(17), 6909-6912. doi: https://doi.org/10.1021/jo801135j
Zhou, J.-L., Liang, Y., Deng, C., Zhou, H., Wang, Z., Sun, X.-L., Zheng, J.-C., Yu, Z.-X., and Tang, Y. (2011). Tunable carbonyl ylide reactions: Selective synthesis of dihydrofurans and dihydrobenzoxepines. Angewandte Chemie International Edition, 50(34), 7874-7878. doi: https://doi.org/10.1002/anie.201100551
Zhou, J.-L., Wang, L.-J., Xu, H., Sun, X.-L., and Tang, Y. (2013). Highly enantioselective synthesis of multifunctionalized dihydrofurans by copper-catalyzed asymmetric [4+1] cycloadditions of α-benzylidene-β-ketoester with diazo compound. ACS Catalysis, 3(4), 685-688. doi: https://doi.org/10.1021/cs400019u

Ayrıntılar

Birincil Dil

Türkçe

Konular

Fiziksel Kimya (Diğer)

Bölüm

Araştırma Makalesi

Yazarlar

Füsun Şeyma Güngör ^*
0000-0003-0870-4048
Türkiye

Ayşe Özdemir
0000-0001-8547-523X
Türkiye

Yayımlanma Tarihi

15 Mart 2024

Gönderilme Tarihi

20 Kasım 2023

Kabul Tarihi

14 Mart 2024

Yayımlandığı Sayı

Yıl 2024 Cilt: 14 Sayı: 1

DOI

https://doi.org/10.31466/kfbd.1393378

IZ

https://izlik.org/JA82DR33CU

APA

Güngör, F. Ş., & Özdemir, A. (2024). α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri. Karadeniz Fen Bilimleri Dergisi, 14(1), 249-261. https://doi.org/10.31466/kfbd.1393378

AMA

1.Güngör FŞ, Özdemir A. α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri. KFBD. 2024;14(1):249-261. doi:10.31466/kfbd.1393378

Chicago

Güngör, Füsun Şeyma, ve Ayşe Özdemir. 2024. “α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri”. Karadeniz Fen Bilimleri Dergisi 14 (1): 249-61. https://doi.org/10.31466/kfbd.1393378.

EndNote

Güngör FŞ, Özdemir A (01 Mart 2024) α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri. Karadeniz Fen Bilimleri Dergisi 14 1 249–261.

IEEE

[1]F. Ş. Güngör ve A. Özdemir, “α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri”, KFBD, c. 14, sy 1, ss. 249–261, Mar. 2024, doi: 10.31466/kfbd.1393378.

ISNAD

Güngör, Füsun Şeyma - Özdemir, Ayşe. “α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri”. Karadeniz Fen Bilimleri Dergisi 14/1 (01 Mart 2024): 249-261. https://doi.org/10.31466/kfbd.1393378.

JAMA

1.Güngör FŞ, Özdemir A. α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri. KFBD. 2024;14:249–261.

MLA

Güngör, Füsun Şeyma, ve Ayşe Özdemir. “α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri”. Karadeniz Fen Bilimleri Dergisi, c. 14, sy 1, Mart 2024, ss. 249-61, doi:10.31466/kfbd.1393378.

Vancouver

1.Füsun Şeyma Güngör, Ayşe Özdemir. α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri. KFBD. 01 Mart 2024;14(1):249-61. doi:10.31466/kfbd.1393378

Karadeniz Fen Bilimleri Dergisinde yayınlanan makaleler Creative Commons Attribution-NonCommercial 4.0 International kapsamında lisanslanmıştır.

α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri

α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri

Öz

Anahtar Kelimeler

Rh2(OAc)4-Catalyzed Reactions of α,β-Conjugated Enon Compounds with 2-Diazo-5,5-Dimethyl-1,3-Cyclohexandione

Öz

Anahtar Kelimeler

Destekleyen Kurum

Proje Numarası

Etik Beyan

Teşekkür

Kaynakça

Ayrıntılar

Birincil Dil

Konular

Bölüm

Yazarlar

Yayımlanma Tarihi

Gönderilme Tarihi

Kabul Tarihi

Yayımlandığı Sayı

DOI

IZ

Kaynak Göster